Paul B White1, Shannon S Stahl. 1. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA
Abstract
Alkene insertion into Pd-N bonds is a key step in Pd-catalyzed oxidative amidation of alkenes. A series of well-defined Pd(II)-sulfonamidate complexes have been prepared and shown to react via insertion of a tethered alkene. The Pd-amidate and resulting Pd-alkyl species have been crystallographically characterized. The alkene insertion reaction is found to be reversible, but complete conversion to oxidative amination products is observed in the presence of O(2). Electronic-effect studies reveal that alkene insertion into the Pd-N bond is favored kinetically and thermodynamically with electron-rich amidates.
Alkene insertion into n class="Chemical">Pd-N bonds is a key step in Pd-catalyzed oxidative amidation of alkenes. A series of well-defined Pd(II)-sulfonamidate complexes have been prepared and shown to react via insertion of a tethered alkene. The Pd-amidate and resulting Pd-alkyl species have been crystallographically characterized. The alkene insertion reaction is found to be reversible, but complete conversion to oxidative amination products is observed in the presence of O(2). Electronic-effect studies reveal that alkene insertion into the Pd-N bond is favored kinetically and thermodynamically with electron-rich amidates.
Authors: Jodie L Brice; Jenna E Harang; Vitaliy I Timokhin; Natia R Anastasi; Shannon S Stahl Journal: J Am Chem Soc Date: 2005-03-09 Impact factor: 15.419
Authors: Paul B White; Jonathan N Jaworski; Charles G Fry; Brian S Dolinar; Ilia A Guzei; Shannon S Stahl Journal: J Am Chem Soc Date: 2016-04-05 Impact factor: 15.419